1-Pentanol → HCID 66799860, compound

HRID 589777Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH3:29]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1

Participants

Reactant 2

HCID 62761-Pentanol

HCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid2×

Product 1

HCID 66799860HCID 66799860, compoundYield 76%

Procedure

The product was prepared from 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19) and 1-pentanol (8.8 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107. The title compound was obtained in 76% yield (18.8 mg). 1H NMR (500 MHz, CDCl3) δ ppm 0.89-0.95 (m, 3 H) 1.32-1.42 (m, 4 H) 1.67-1.75 (m, 2 H) 2.45 (s, 3 H) 4.26 (t, J=6.77 Hz, 2 H) 6.87 (s, 1 H) 7.36 (dd, J=8.10, 7.63 Hz, 1 H) 7.42 (ddd, J=8.10, 2.36, 1.25 Hz, 1 H) 7.44 (dd, J=8.70, 1.95 Hz, 1 H) 7.69-7.73 (m, 3 H) 7.84 (ddd, J=7.63, 1.50, 1.25 Hz, 1 H). MS (ESI+) m/z 452 [M+H]+.

Sources & evidence

ORD record: ord-82885bdbd86a46d9b4bb940060e74e99
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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